New Windsor, NY Homes

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  /47

  $725,000

  $50K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,488 Sq Ft

  2723 Colonial Dr, New Windsor, NY 12553

  Welcome to 2723 Colonial Drive in New Windsor—offering over 2,400 sq ft of living space, 4 bedrooms, and 2.5 bathrooms in a convenient Hudson Valley location. The main level features a bright layout with spacious living areas, a fireplace, and an eat-in kitchen designed for everyday living and entertaining. A first-floor office/den provides added flexibility. The lower level offers additional

  Felix Pena RE/MAX Benchmark Realty Group

  2723 Colonial Dr, New Windsor, NY 12553
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  /13

  $1,150 Per Month

  • 1 Bed
  • 1 Bath
  • 872 Sq Ft
  • Apartment for Rent

  2415 New York 32 Unit 5, New Windsor, NY 12553

  Cozy 1-bedroom, 1-bath apartment available for rent. This modest unit offers a functional layout with a living area, separate bedroom, full bathroom, and kitchen with basic appliances. The apartment is an affordable and easy-to-maintain living space. Conveniently located near local shops, restaurants, and public transportation. On site parking. NO PETS, NO EXCEPTIONS. PLEASE DO NOT ASK. Tenant is

  Guy Cusumano Howard Hanna Rand Realty

  2415 New York 32 Unit 5, New Windsor, NY 12553
• 

  $239,000

  Sold Jan 16, 2026

  223 Brittany Terrace, Rock Tavern, NY 12575

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 2015

  Last Sold Summary

  • $142/SF
  • 87 Days On Market

  Last Listing Agent Sandra Spector Howard Hanna Rand Realty

  223 Brittany Terrace, Rock Tavern, NY 12575
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  Est $275,121

  Not Listed For Sale

  276 Temple Hill Rd Unit 2510, New Windsor, NY 12553

  • 2 Beds
  • 2 Baths
  • 1,180 Sq Ft
  • Built 1986

  276 Temple Hill Rd Unit 2510, New Windsor, NY 12553

  Last Sold Summary

  • 24 Days On Market
• 

  

  

  /41

  $489,000

  New Construction Pending

  • 3 Beds
  • 3 Baths
  • 1,248 Sq Ft

  111 Cedar Ave, New Windsor, NY 12553

  Welcome to this beautifully crafted NEW CONSTRUCTION home in the desirable New Windsor area, showcasing a clean, modern design throughout! This thoughtfully designed residence offers 3 spacious bedrooms, 1 full bathroom, and 2 half bathrooms, including a convenient first-floor powder room. Step inside to find gleaming hardwood floors and a bright, open layout enhanced by a sleek, contemporary

  Waldina Almazan RE/MAX Benchmark Realty Group

  111 Cedar Ave, New Windsor, NY 12553
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  /4

  $3,500 Per Month

  • 4 Beds
  • 3 Baths
  • 2,078 Sq Ft
  • House for Rent

  12 Union Ave, New Windsor, NY 12553

  Very spacious home with large bedrooms completely remodeled, beautiful hardwood floors, central air conditioning, gas heat, situated just off Route 9W makes easy access for commuter. Short drive to West Point Military Academy, Harriman State Park, Salisbury Mills train line. Beautiful yard to enjoy and wrap around deck makes for great gatherings. This house will rent fast! Parking for 3 to 4

  Maureen Arias Keller Williams Realty Partner

  12 Union Ave, New Windsor, NY 12553
• 

  $395,000

  Sold Nov 13, 2025

  402 Plover Ct, New Windsor, NY 12553

  • 2 Beds
  • 2 Baths
  • 1,502 Sq Ft
  • Built 2000

  Last Sold Summary

  • 3% Above List Price
  • $263/SF
  • 37 Days On Market

  Current Estimated Value $397,654

  Last Listing Agent Sharon Satkowski Hudson Heritage Realty

  402 Plover Ct, New Windsor, NY 12553
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  Est $289,995

  Not Listed For Sale

  276 Temple Hill Rd Unit 2705, New Windsor, NY 12553

  • 2 Beds
  • 2 Baths
  • 1,176 Sq Ft
  • Built 1986

  276 Temple Hill Rd Unit 2705, New Windsor, NY 12553

  Last Sold Summary

  • 22 Days On Market
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  /46

  $699,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,276 Sq Ft

  3510 John Paul Jones Ln, New Windsor, NY 12553

  Welcome to this stunning 4-bedroom, 2.5-bath home located in The Reserve, New Windsor, offering breathtaking panoramic views and exceptional living space throughout. This beautifully maintained home features oak flooring, an inviting eat-in kitchen with custom cabinetry, granite countertops, and stainless steel appliances.The spacious living room just off the kitchen is perfect for

  John Ruggieri BHHS Hudson Valley Properties

  3510 John Paul Jones Ln, New Windsor, NY 12553
• 

  $211,000

  Sold Sep 15, 2025

  115 Chestnut Ave, New Windsor, NY 12553

  • 2 Beds
  • 1 Bath
  • 985 Sq Ft
  • Built 1953

  Last Sold Summary

  • 3% Below List Price
  • $214/SF
  • 20 Days On Market

  Current Estimated Value $247,760

  Last Listing Agent Brian Smith River Realty Services, Inc.

  115 Chestnut Ave, New Windsor, NY 12553
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  Not Listed For Sale

  810 Blooming Grove Turnpike Unit 26, New Windsor, NY 12553

  • 1 Bed
  • 1 Bath
  • 952 Sq Ft
  • Built 1965

  810 Blooming Grove Turnpike Unit 26, New Windsor, NY 12553

  Last Sold Summary

  • 41 Days On Market
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  /19

  $489,750

  • 3 Beds
  • 2.5 Baths
  • 1,876 Sq Ft

  47 Continental Dr, New Windsor, NY 12553

  Welcome home to this beautifully updated raised ranch nestled in one of New Windsor’s quiet and established neighborhoods. Set on nearly half an acre, this 3-bedroom, 2.5-bath home offers the perfect combination of comfort, space, and modern updates. Step inside to discover thoughtfully renovated living spaces filled with natural light and designed for everyday living. Several updated rooms

  James LaTempa Compass Greater NY, LLC

  47 Continental Dr, New Windsor, NY 12553
• 

  $305,000

  Sold Aug 25, 2025

  1025 Washington Green, New Windsor, NY 12553

  • 2 Beds
  • 2 Baths
  • 1,029 Sq Ft
  • Built 1989

  Last Sold Summary

  • 2% Below List Price
  • $296/SF
  • 41 Days On Market

  Current Estimated Value $308,199

  Last Listing Agent Edgar Meza Keller Williams Village Sq Rlt

  1025 Washington Green, New Windsor, NY 12553
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  Not Listed For Sale

  187 Bethlehem Rd, New Windsor, NY 12553

  • 5 Beds
  • Built 1947

  187 Bethlehem Rd, New Windsor, NY 12553

  Last Sold Summary

  • 5 Days On Market
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  /14

  $99,900

  New Construction

  • 2 Beds
  • 2 Baths
  • 784 Sq Ft

  11 Square Hill Rd Unit 27, New Windsor, NY 12553

  Amazing end lot with privacy! Imagine your bright and modern new home, ready this spring! This lovely home offers comfort, convenience and affordability. The home features a bright and airy open layout. The kitchen cabinets are white and it offers a crisp contemporary feel with tons of cabinets and appliances. You'll find two nice bedrooms situated on opposite ends of the home, offering privacy.

  Sandra Spector Howard Hanna Rand Realty

  11 Square Hill Rd Unit 27, New Windsor, NY 12553
• 

  $500,000

  Sold Oct 23, 2025

  419 Philo St, New Windsor, NY 12553

  • 3 Beds
  • 2 Baths
  • 1,894 Sq Ft
  • Built 1973

  Last Sold Summary

  • 1% Above List Price
  • $264/SF
  • 31 Days On Market

  Current Estimated Value $498,876

  Last Listing Agent Kelly Campbell Century 21 Alliance Rlty Group

  419 Philo St, New Windsor, NY 12553
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  Not Listed For Sale

  30 Meriline Ave, New Windsor, NY 12553

  • 4 Beds
  • 2 Baths
  • 1,610 Sq Ft
  • Built 1900

  30 Meriline Ave, New Windsor, NY 12553

  Last Sold Summary

  • 224 Days On Market
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  /47

  $499,900

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,020 Sq Ft

  14 Creamery Dr, New Windsor, NY 12553

  Welcome to 14 Creamery Drive, a beautifully maintained and thoughtfully updated split-level home ideally situated in the town of New Windsor and within the highly sought-after Cornwall school district. Offering the perfect balance of comfort, functionality, and modern upgrades, this home is move-in ready with major improvements completed for peace of mind. The home showcases a series of important

  Ruth Garcia Keller Williams Prestige Prop

  14 Creamery Dr, New Windsor, NY 12553
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  $415,000

  Sold Jan 12, 2026

  36 Moores Hill Rd, New Windsor, NY 12553

  • 2 Beds
  • 1.5 Baths
  • 2,193 Sq Ft
  • Built 1954

  Last Sold Summary

  • 4% Above List Price
  • $189/SF
  • 24 Days On Market

  Current Estimated Value $435,973

  Last Listing Agent Tracy Lockhart RE/MAX Benchmark Realty Group

  36 Moores Hill Rd, New Windsor, NY 12553
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  Not Listed For Sale

  31 Beakes Rd, New Windsor, NY 12553

  • 6 Beds
  • 3.5 Baths
  • 3,410 Sq Ft
  • Built 1930

  31 Beakes Rd, New Windsor, NY 12553

  Last Sold Summary

  • 71 Days On Market
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  /11

  $245,500

  $4K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,280 Sq Ft

  27 Lexington Ln, New Windsor, NY 12553

  Your new home awaits you in the Squire Village community in New Windsor NY! Located with easy access to the Beacon Newburgh bridge, to Beacon Metro North train station and effortless access to 9W directly to West Point! This 1,280 sq ft, townhome has 3 bedrooms and plenty of space for you and your family. Freshly painted and ready for you to move right in. Some updates have been done, This unit

  Sean McPhail Next Level Property Management

  27 Lexington Ln, New Windsor, NY 12553
• 

  $480,000

  Sold Oct 15, 2025

  510 MacNary Rd, New Windsor, NY 12553

  • 3 Beds
  • 2.5 Baths
  • 2,158 Sq Ft
  • Built 1975

  Last Sold Summary

  • 7% Above List Price
  • $222/SF
  • 18 Days On Market

  Current Estimated Value $492,021

  Last Listing Agent Thomas Lawrenson Howard Hanna Rand Realty

  510 MacNary Rd, New Windsor, NY 12553
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  Not Listed For Sale

  818 Mount Airy Rd, New Windsor, NY 12553

  • 6 Beds
  • 3.5 Baths
  • 2,777 Sq Ft
  • Built 1930

  818 Mount Airy Rd, New Windsor, NY 12553

  Last Sold Summary

  • 185 Days On Market
• 

  

  /18

  $395,000

  Pending

  • 3 Beds
  • 1 Bath
  • 1,438 Sq Ft

  85 Holloran Rd, New Windsor, NY 12553

  Cornwall Schools and newly remodeled cape cod home features over 1,400 sq. ft., 3 bedrooms and one full bath with additional space for and office and a den. New roof, brand new gorgeous hard wood floors throughout, spacious level lot with above ground pool. Close to five corners, restaurants, eateries, grocery stores, schools, shops and banks. West Point and Woodbury Premium outlets are a

  Kathleen Rafferty RE/MAX Benchmark Realty Group

  85 Holloran Rd, New Windsor, NY 12553
• 

  $265,000

  Sold May 12, 2026

  70 Meadowbrook Ln, New Windsor, NY 12553

  • 3 Beds
  • 1 Bath
  • 1,525 Sq Ft
  • Built 1940

  Last Sold Summary

  • 18% Below List Price
  • $174/SF
  • 73 Days On Market

  Current Estimated Value $418,667

  Last Listing Agent Paul Biagini Biagini Realty

  70 Meadowbrook Ln, New Windsor, NY 12553
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  Est $581,934

  Not Listed For Sale

  1629 State Route 94, New Windsor, NY 12553

  • 4 Beds
  • 2 Baths
  • 1,836 Sq Ft
  • Built 1917

  1629 State Route 94, New Windsor, NY 12553

  Last Sold Summary

  • 33 Days On Market
• 

  

  /50

  $499,900

  • 3 Beds
  • 2.5 Baths
  • 1,513 Sq Ft

  28 Park Hill Dr, New Windsor, NY 12553

  Welcome to this beautifully maintained and extensively upgraded 3-bedroom, 2.5-bath raised ranch with an incredible backyard oasis featuring a stunning in-ground pool — just in time for summer. Over the past three years, significant improvements have been made to transform this property into the perfect place to call home, including a new roof, siding, hot water heater, sump pump, renovated

  Danielle Raguzin Re-Max Experience

  28 Park Hill Dr, New Windsor, NY 12553
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  $660,000

  Sold Feb 18, 2026

  34 Melissa Ln, Washingtonville, NY 10992

  • 3 Beds
  • 2.5 Baths
  • 2,600 Sq Ft
  • Built 1998

  Last Sold Summary

  • 8% Below List Price
  • $254/SF
  • 180 Days On Market

  Current Estimated Value $663,335

  Last Listing Agent Mary Ann Mitchell eXp Realty

  34 Melissa Ln, Washingtonville, NY 10992
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  Est $440,667

  Not Listed For Sale

  692 Mount Airy Rd, New Windsor, NY 12553

  • 2 Beds
  • 1.5 Baths
  • 1,460 Sq Ft
  • Built 1970

  692 Mount Airy Rd, New Windsor, NY 12553

  Last Sold Summary

  • 56 Days On Market
• 

  

  /23

  $1,500,000

  • Land
  • 29 Acres
  • $51,724 per Acre

  0 Mt Airy Rd Unit KEY913137, New Windsor, NY 12553

  Be a visionary! This is 29 acres in the Hudson Valley—prime land where luxury living meets unmatched opportunity. Picture a new community of high-end homes, an equestrian estate development, or a luxury retreat destination. With open meadows, mature woodlands, and multiple building sites with ample frontage, the groundwork is already here. This property offers privacy and natural beauty—yet it’s

  Donna Ramundo Keller Williams Valley Realty

  0 Mt Airy Rd Unit KEY913137, New Windsor, NY 12553
• 

  $590,000

  Sold May 28, 2026

  5 Sunrise Terrace, New Windsor, NY 12553

  • 4 Beds
  • 2.5 Baths
  • 1,968 Sq Ft
  • Built 1950

  Last Sold Summary

  • 7% Above List Price
  • $300/SF
  • 29 Days On Market

  Current Estimated Value $539,211

  Last Listing Agent Zachary Crosby

  5 Sunrise Terrace, New Windsor, NY 12553
• 

  Est $800,000

  Not Listed For Sale

  290 Toleman Rd, Washingtonville, NY 10992

  • 3 Beds
  • 3.5 Baths
  • 3,205 Sq Ft
  • Built 1998

  290 Toleman Rd, Washingtonville, NY 10992

  Last Sold Summary

  • 39 Days On Market
• 

  

  /35

  $205,900

  $14K PRICE DROP Pending

  • 2 Beds
  • 1.5 Baths
  • 1,200 Sq Ft

  10 Oakwood Terrace Unit 38, New Windsor, NY 12553

  Tucked away in a quiet corner of New Windsor’s Oakwood Crest coop community, this lovely 2-bedroom duplex-style home offers comfort, space, and convenience. Enjoy relaxing on your private patio during warm summer evenings or entertaining with ease thanks to the home’s open-concept kitchen and dining area—perfect for everyday living or casual get-togethers. Step inside to find brand new carpeting

  Steve Vinti Weichert Realtors

  10 Oakwood Terrace Unit 38, New Windsor, NY 12553
• 

  $450,000

  Sold Dec 09, 2025

  303 Windsor Hwy, New Windsor, NY 12553

  • 2 Beds
  • 1 Bath
  • 600 Sq Ft
  • Built 1938

  Last Sold Summary

  • $750/SF
  • 0 Days On Market

  Current Estimated Value $457,974

  Last Listing Agent Joel Lowy MS Realty Group USA, Inc

  303 Windsor Hwy, New Windsor, NY 12553
• 

  Est $784,000

  Not Listed For Sale

  4 Trotter Ln, Rock Tavern, NY 12575

  • 4 Beds
  • 2.5 Baths
  • 2,960 Sq Ft
  • Built 2009

  4 Trotter Ln, Rock Tavern, NY 12575

  Last Sold Summary

  • 23 Days On Market
• 

  

  /33

  $1,100,000

  $150K PRICE INCREASE

  • 4 Beds
  • 3 Baths
  • 3,100 Sq Ft

  4 Jefferson Ave, New Windsor, NY 12553

  CORNWALL SCHOOLS ~ TO BE BUILT BY LOCAL ESTABLISHED REPUTABLE BUILDER ON THIS BEAUTIFUL PRIVATE LOT WITH VIEWS ON 5.1 ACRES. New construction & to be completed in 2026 approximately 9 months after fully executed contracts, weather permitting . Time to customize w/own colors. Approximately 3100' sq. ft. with central air throughout, 4-bedroom, 3 full bathroom colonial. Finished 344' sq. ft. bonus

  George Koudounas RE/MAX Benchmark Realty Group

  4 Jefferson Ave, New Windsor, NY 12553
• 

  $685,000

  Sold Jan 14, 2026

  323 Sycamore Dr, New Windsor, NY 12553

  • 4 Beds
  • 3.5 Baths
  • 3,512 Sq Ft
  • Built 1986

  Last Sold Summary

  • 2% Below List Price
  • $195/SF
  • 74 Days On Market

  Current Estimated Value $691,713

  Last Listing Agent Haakim Byrd HomeSmart Homes & Estates

  323 Sycamore Dr, New Windsor, NY 12553
• 

  Est $406,245

  Not Listed For Sale

  1123 Balsam Dr, New Windsor, NY 12553

  • 2 Beds
  • 2.5 Baths
  • 1,722 Sq Ft
  • Built 2009

  1123 Balsam Dr, New Windsor, NY 12553

  Last Sold Summary

  • 26 Days On Market
• 

  

  /16

  $337,000

  $3K PRICE DROP Pending

  • 3 Beds
  • 1.5 Baths
  • 1,530 Sq Ft

  276 Temple Hill Rd Unit 2808, New Windsor, NY 12553

  Welcome Home to this beautiful 3 bedroom, 1.5 bath end unit! Next to new everything! Washer and dryer in unit, storage, deck and so much more! Make an appointment today to check it out!

  Kelly Roebuck Curasi Realty, Inc.

  276 Temple Hill Rd Unit 2808, New Windsor, NY 12553
• 

  $370,000

  Sold Feb 10, 2026

  11 Hudson Dr, New Windsor, NY 12553

  • 4 Beds
  • 2 Baths
  • 1,408 Sq Ft
  • Built 1960

  Last Sold Summary

  • 1% Above List Price
  • $263/SF
  • 54 Days On Market

  Current Estimated Value $377,103

  Last Listing Agent Alexander Panet Real Broker NY LLC

  11 Hudson Dr, New Windsor, NY 12553

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